The End-of-Year Checklist

I like starting the year with an empty to-do list and a fresh perspective. As an obsessive list maker, this process naturally starts with another list. Some of the questions can be treated as action items, but many require deeper reflection (perfect for the quiet week at the end of the year). I hope that you find it useful as you close out your year!

As a Company

• What actions most moved the company forward and how can we double down on them? What should we have spent less time doing?
  — Using the Pareto Principle, the return on certain actions will significantly outweigh others.
• Did our actions reflect our values? Did we call out times that employees personified our values? Do we need to add or subtract values?
• Which relationships are most important to our success (e.g. customers, investors, partners) and what can we be doing to provide them with more value?

As a Manager

• Do we have the right people on the bus?
• Are the right people owning the right things or are there better ways that we can be distributing the work?
• How were my 1:1s? Did my reports walk away feeling that I had removed blockers, clarified vagueness, and given clear instructions?
• Do my reports know their metrics for success?
• How connected is the team overall?

Meetings

• Is every meeting on my calendar still relevant and useful?
• Have I invited the right people to each one?
• Are the major meetings for the upcoming year already scheduled? Mine are:
  • Off-sites
  • Customer business reviews
  • Employee reviews
  • Team town halls
  • Quarterly kickoffs
  • Annual trainings
• Do I like the cadence and timing of my recurring meetings?
• Can I schedule any back-to-back to minimize distractions?
• Are meetings optimized to my energy peaks?
  • I’m fresh and driven in the mornings, so I schedule mentally challenging meetings during this window.
  • My mind is more relaxed and able to freely relate in the afternoon; I shift most brainstorming meetings to this time.

Tools

• Are we using the right tools (software, banking, equipment, etc.) to accomplish our goals? Can we eliminate any?
• Do the right people have access to each tool? Has admin access been given to the logical person?
• Do we have the right tier of service for our size?
• Are there more effective tools available that could reduce or combine the efforts of others?

Finance

• Are our finances generally in order? This can include:
  • Outstanding invoices
  • Unpaid bills
  • Sales commissions
  • Expense reconciliation
  • Credit card charges
• Are there areas where we could cut costs next year?
• Is billing set to preferred person and method? (I like to see every charge come through and to optimize points based on spend.)

Operations

• Where can we automate tasks?
• Are the company files clean and organized? What about mine?
  • If a company file no longer seems relevant, I dump it into an archive folder rather than delete anything.
  • I run an inbox-zero on my file downloads and desktop, forcing myself to put any important files somewhere safe in case something happens to my computer.
• Are our templated documents up to date?
  • Check company address, point of contact, and legalese on contracts, mNDAs, etc.
• How are our processes? Which ones are sloppy, overly prescriptive, or begging to be eliminated entirely?

Performance

• How did I perform against my job description?
  • I keep my job description as a living document to capture what I take on and hand off over time. When I think my time could be better spent, I discuss this document with my boss and adjust accordingly.
• How were my 1:1s with my boss? Did I come to the meeting with thoughtful questions and specific to-dos?
• Did I listen to and incorporate feedback effectively?
• Did I step up when I needed to? Did I delegate my areas of weakness?

Role

• How do I want my job description to change in the next year based on what the company needs and on my own strengths and weaknesses?
• Which relationships within the company are most important to my efficacy? Can I do anything to improve upon those relationships?
• Which tasks should I be taking on or offloading?

Time

• Am I spending time on the most valuable things and letting the unimportant things fall through the cracks?
• What have I been putting off?
  • Can I eliminate it or delegate it?
  • Can I give it more clarity?
• What can I stop doing altogether?

Personal

• Do I like my personal systems for keeping track of to-dos?
• Do I know what I bring to the table when I join a meeting?
• Am I maintaining a network of people I can turn to for advice?
• Am I making time outside of work for activities that keep me healthy and happy?

Originally published in November 2020